Canada
Gairey moved to Toronto from Cuba in August 1914. He worked for the Grand Trunk Railway as a dishwasher, cook, and waiter until 1932, when Black waiters were laid off in the competition for remaining jobs resulting from the railway's absorption into the operations of Canadian National Railway. He married a Hindu Jamaican dressmaker, Elma, and they had a son, Harry Junior. In 1936, to support his family, Gairey returned to railway work, this time for Canadian Pacific Railway as a porter. The poor working conditions and lack of job security led Gairey, along with other porters including Stanley G. Grizzle, to form a local chapter of the Brotherhood of Sleeping Car Porters labour union in the 1940s. Gairey was promoted to the position of porter instructor in the late 1940s.
In November 1945 Gairey's teenage son, Harry Gairey Jr., was refused entry to the Icelandia indoor skating rink because of his race. The incident and resulting protests by students received substantial news coverage in Toronto. Gairey appealed to his alderman and city council, spurring the creation of Toronto's first anti-discrimination ordinance in 1947. Gairey argued that since conscription applied to all young Canadian men, regardless of race, the rights of every citizen should be the same as well.
Gairey's civil rights activism made him a leader in the Toronto Black community and effected change at a national level. Inspired by the work of Marcus Garvey, he was a charter member of the Toronto branch of the Universal Negro Improvement Association and helped to form the Negro Citizenship Association to advocate for changes to Canada's discriminatory immigration law.
In an obituary, Gairey was lauded for his leadership and his efforts to combat racial discrimination.
